


Literally In Your Dreams

by HeroFizzer



Category: Fate/Grand Order
Genre: Anal, Crossdresser, M/M, Other, dream - Freeform, trap
Language: English
Status: In-Progress
Published: 2018-10-08
Updated: 2019-05-19
Packaged: 2019-07-28 09:18:59
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,755
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16238684
Author URL: https://archiveofourown.org/users/HeroFizzer/pseuds/HeroFizzer
Summary: What does one do when they want to write about a character but not get bogged down by the major continuity of their series?Write it anyway :P





	1. Chapter 1

You look over at the time, noticing just how late it is. Three AM, and here you are, sitting at your computer desk, making an attempt to write this story about a character you barely even know anything about.

You pull up their picture again, sighing as your eyes remain glued to the pink haired subject. It always surprises you that this Astolfo, as he's called, is a crossdresser, just because of how feminine and adorable he looks. It's unlike any other that you've seen in most anime, although that really isn't an accomplishment given how little you've watched since high school. Then again, the number of known traps in the media off the top of your head isn't very high, either. But still, this little piece of cheerful fluff keeps popping up wherever you look, and you're trying to get it out of your head by writing a story about them and hoping he'll leave your mind finally.

There's just one problem; you don't find the source they're attached to all that interesting.

Let's be frank; you don't know, or care for that matter, about this Fate series, because nothing else really sticks out for you, bar a scene you found where one of the female characters discovers Astolfo's actual gender. Understandable, given how cute he dresses in and out of battle, but this series has way too many characters to count, and it's apparently so big you have no idea where to even start. Not to mention the backlog of other shows and games you need to play through on your own time...

You run your hand over your tired eyes, which squint as they stare at the blank document on your computer screen. You can't think of a premise, yet you know you should be trying to understand the greater universe Astolfo is apart of. But you don't have that kind of time, and you really only care about this one particular individual. You just want to write about him.

“Then just do that.”

Out of shock, you spin around in your chair, eyes wide to find the pink haired, snaggle-toothed trap kneeling atop your sofa, a devilish grin on his lips. Your eyes notice that he's wearing that outfit you first found him in, that pink sailor outfit that you still don't understand the context of, yet it shows off the more feminine of his features. “Wh-What? Wait, you can't be real!” you shout, slowly rising out of your desk chair.

“Of course I'm not real!” Astolfo says, giggling. “You fell asleep like five hours ago, dude. You should see the actual document, nothing but 'k's for fifty pages right now.”

You shake your head, preparing to pinch yourself to make sure you are in fact dreaming. Before doing so, you realize that would end the dream, and you might just have a clue where all of this is going. “Okay, wait, you mentioned that I should just...write about you?” You pause as Astolfo nods his head, his hands resting atop his schoolgirl skirt while you notice a small bulge poking up from underneath. “Yeah, that...that doesn't seem as easy as you'd think.”

Cocking his head to the side, Astolfo blinks in a way to show he doesn't understand. “Nani? What do you mean not as easy?”

You sit down next to him, your eyes looking down at the hard wood floor while the pink haired trap rests his arms and head on your shoulder, awaiting the explanation. “Look, I like to do a lot of research when it comes to stuff like yourself. You know, get a grasp on the character, their surroundings, and build a story off of that. But I don't have the care to get into your source material like I would with, say, RWBY or DxD. Like there's more than one character involved in all of that that makes it intriguing, but you...you've kind of surpassed your home franchise.”

“Have I? Neat!” Astolfo says with a grin, his hand slowly running down your chest without you realizing it, too focused on everything else to care.

“I guess,” you say, “but that just makes getting into your series a little harder, especially since you're in like, what, two or more things?”

Astolfo giggles, his hand now rubbing over your crotch. “Dude, you need to relax. I get it, you want your writing to be awesome and picked up by the fans and get their attention. You want to show you care about the characters you write. You want to prove you get the thing, but you can't always let it consume you. I mean that doesn't stop you from the Overwatch stuff, does it? It's not like everything is concrete yet.”

“You're not wrong...” you sigh, eyes shut as you feel his palm massaging your thighs through your pants.

“I think your readers will understand, just this once,” Astolfo says, now leaning into your ear to whisper, his breath against your ear drums, “that you wanna write about a cute guy like me and not give a damn about anything else. So just do it.” You then tilt your head as the pink haired trap presses his lips against your neck, causing a sigh of pleasure to escape your mouth. His hand continues to press against your lap as your member grows, pushing against your pants as the trap's palm finally finds the tip of your erection. Nuzzling against your neck, feeling his saliva on his cheek, the crossdresser uses his hands to unzip your fly, pulling out your cock and feeling its girth in his hand. His eyes look down to see the physical size of your member, nothing too spectacular, though above average. This being your dream, he's not too concerned with the size, just being overly aroused for you. As you turn your head to face him, you're surprised to feel his lips against yours, eyes shut as you accept his kiss, breathing through your nostrils from the unexpected embrace of the trap. You feel his tongue push into your mouth, pushing against your own for his own amusement while he continues to stroke away at your rod, his thumb pushing down on your tip, squishing down on the slit.

“Does it feel good?” Astolfo asks, briefly breaking the kiss with a strand of saliva between your lips. He of course refers to the way his hand massages your cock, his hand tightly around your member as he gives it repeated strokes. “C'mon, it does, doesn't it? You must really like the idea of a trap like me giving you so much attention and sexual pleasure.”

"Yeah, guess I do." you respond, so lost in his touch that he could day literally anything and you'd agree with it. His lips go back to yours, moaning as he pushes into your chest, your upper body rolling with it and laying atop your sofa. The pink haired crossdresser grins at you, still stroking away at your member with his thumb pushing down on the side in an attempt to shoot a dab of precum out of your slit. You watch as a little dab of the liquid oozes out, which he smoothes with his thumb, moving it around your crown as if to lubricate it. His eyes look down at your cock for a brief moment, watching as your head glistens in the light bouncing off your computer screen.

Leaning into your body, with his skirt covered ass sticking up in the air, Astolfo leans into your lap, his tongue out at the base of your pole. Licking his way upwards, you let out a heavy sigh as the crossdresser leaves a trail of saliva on the underside, making his way up to your tip. When he reaches the top of your cock, his mouth opens up wide, swallowing your pink nub whole, humming as he flicks away at the sensitive portion of your erection. Looking up as he continues to use his mouth on you while his tooth lightly drags across your skin, he notices the way you grab onto the side of the sofa cushions, your eyes shut as you breathe heavily from his way of giving you head. After popping his lips off, Astolfo asks you, "See, this isn't so bad, is it? Getting your cock worked on by little old me?" He begins to flick his tongue away at the slit, lapping up any precum that oozes out.

"It's nice…" you reply, enjoying the sensation more than you imagined. As you watch his lips move back to your member, slowly suckling away at the tip, you can't help but notice the black bows in his hair, formulating a use for them in your mind. Reaching out for the hair decorations, you pull on them, bringing Astolfo's head all the way down your rod, with the crossdresser's eyes widening with surprise. Just as quickly he gives you a mischievous look and a muffled cackle, as if he had wanted you to get aggressive with him this whole time. You watch as his head bobs up and down your shaft, all the while keeping a hold on his bows to bring him back down to the base. After a while, you take in a deep breath, biting your lower lip as your rod swells up, the veins pumping in more blood for the inevitable orgasm, all courtesy of Astolfo's fantastic blow job.

Letting go of Astolfo's bows as he brings his head up, he swings too far back expecting you to hold him down. With his lips removed from your rod, he looks down at the slit, shutting his eyes the second he sees the white milky substance make its escape. Already he feels your seed splash onto his face, making an immediate mess as your load blasts atop him, covering his nose and cheeks in your fluids, though he tries his best to keep his mouth open to catch some of the jizz.

As you sit yourself up properly, you get a good glimpse of Astolfo's face, looking at his glazed expression while his tongue licks up your seed around his lips. As he keeps the rest of your cum on him, the crossdresser smiles adorably, saying to you, “I'm still pretty, right?”

You laugh, “Yeah, you're definitely pretty.” Even with his face coated in jizz, he crawls up to you, showing off your semen as it rests atop his tongue, as if the trap is willing to share your taste with him. Taking the bait, you lean in to meet with him, lips locking as he pushes his tongue inside your mouth yet again, only this time allowing you the opportunity to take in the spunk you made. Even as you swallow, you move about the crossdresser's face, licking off bits of your seed to share back with him, assuring that he has a taste of you to take down as well.

But you don't stop there. You remove Astolfo's sailor top, much to his surprise, though he moans in such a harmonious tone when your thumbs press against his tiny nipples. Your lips move onto his neckline while the pink haired young man holds you close with one arm, while he bites down on his knuckle. Your hand moves down his slender yet fit body, amazed that someone like himself can be so feminine in design. Your amazement wears off quickly as you move your hand under the hem of his skirt, sliding around his tiny hips until you find the button that keeps the clothing in place, undoing it to remove it from his torso. With Astolfo now naked on your couch, you flip him over so that his legs are raised over his head while he falls on his back. Though taken by surprise, the pink haired young man soon gives you his toothy grin, telling you, “Do it.” as he spreads his ass cheeks apart, his five inch cock slowly rising up.

While you hold onto Astolfo's thighs, you jut your hips into him, your rod poking at his asshole. With a harsh thrust you manage to push inside his cute little entry point, causing his face to contort as he growls through clenched teeth. “Oh fuck! Yes! Just like that!” he begs, burying his face into your shoulder as you lay on top of him. “Fuck my boy pussy, you jerk! Make me your little bitch!” You only wish you could see his face right now, how it must look while he begs you to continue pounding his asshole while you massage his prostate so thoroughly. When he pulls back from your shoulder, you get a glimpse of the glazed look in his eyes, begging you to keep going, while also feeling a small portion of your skin dug into on the neckline. You figure it's only from the pink haired young man's tooth and move on, too fixated on wanting to fill his ass up with your cum. You can't hold back any longer, wanting that sweet release you've been wanting with him for so long.

“Fuck me...” Astolfo squeaks, his hands grabbing onto the sofa as best he can while wrapping his legs around your torso. “Yes, that's it! Fuck me good! Keep going, you bastard! Fill my ass with your jizz! I wanna feel like a cum dumpster with you!” You feel as though he may be overexaggerating, though you do need to remind yourself that this is all a dream, and anything is possible.

With one hard thrust, you hold your body against Astolfo's, watching his eyes grow wide as you release your seed within his boy pussy, seeing his teeth clench together in beautiful agony. His hand grabs for his own member, watching him tug away as your jizz still fills his hole up, doing your best to see the cute little orgasm he has at the same time. The way he cums with little drops of semen landing on his chest doesn't measure up to the gallons you offer him, but you expect it of someone who seems to accept his role as a bottom so easily.

When you finish, you pull out of Astolfo's ass, watching as the pink haired crossdresser pushes part of your load out of his anus, breathing heavily while his face and toned stomach are covered in cum. “So...” you say, wiping off your forehead, “that was totally worth it.”

With a weak smile on his face, Astolfo says to you, “Totally worth getting done and over with, right?”

“Yup. Got a lot out of my system.” After you sit upright on the couch, your head tilted back to face the ceiling, Astolfo rests his cum covered cheek on your arm, holding you close. "Does make me wish the dream wouldn't end, though."

"Oh, don't worry." Astolfo says, looking up at you to wink for your attention. "I'm pretty sure this won't be the only dream you have of me."


	2. Chapter 2

You find yourself seated at what looks to be a fancy looking restaurant, with a meal planted right in front of you. The plate looks indecipherable, as if your mind can't properly decide what it's meant to be exactly. Spaghetti? A salad? It's something you would associate with Italian cuisine, but nothing seems to settle. You also notice that your table is square in the middle of the room, with everyone else's tables up against the wall, leaving plenty of room for others to be seated around you. Yet here is all this empty space, with nothing being done with it. It all comes across so strangely...

Then you realize that there's nobody here with you. The seat across from you is completely empty, with no sign that there's anyone with you; no purse, no coat, no anything, though you wonder why your mind immediately jumps to a female person. Then you turn your head when you hear someone walk in, with a cheerful feminine voice shouting, “Sorry I'm late!”

Once you see who it is apologizing to you, your eyes go wide. Whether that has to do with the person addressing you or what they're wearing, you're not sure. All you know is that they look stunning.

Astolfo approaches your table, showing off the outfit that he wears with a quick spin on his heel. His footwear is a pair of black ankle high boots with no heel, likely made for comfort on his part, while the dress goes down to his thighs, though the spin gives enough air to show off the cotton panties underneath. The dress itself is a sparkly silver that has backless exposure, going down to just above his backside. It attaches to a black rim that fits like a necklace around his neck, while the Black Rider's face and hair remain unchanged, sticking to its trademark pink braids.

“You know, you wouldn't think I'd be running so far past some made up time for a dream date...” Astolfo says, seating himself at your table. “But here I am, doing exactly that. Is that some sort of fantasy of yours when it comes to dating?”

“...Dammit, I'm dreaming again, aren't I?” you realize.

“So up on the uptake.” Astolfo says with a giggle. “I did just mention 'dream date' didn't I? And the fact I'm here didn't tip you off already?” The crossdresser rests his cheeks onto his fists, giving you a devilish smirk while his fang sticks out of his mouth.

“It should've, sure.” you say. “So, I guess I feel a little weird about asking this, but...why am I dreaming about you again? It's been quite a few months since the last time, and I swear I haven't had any dreams between then and now.”

“I'm guessing you have another mini-obsession about me.” Astolfo says in a teasing manner, running his finger over the rim of his champagne glass. “I can't really say I blame you, seeing as I'm the best looking in my cast.”

“In fairness you're the only person I even know -from- your cast.” you say.

“Nothing wrong with that!” Astolfo says with a laugh. It's oddly loud enough that you would expect the distant patrons to hear him, and yet no one pays you the least bit of attention. “It just means when you think of Fate you immediately think of me~! It's pretty flattering.”

“Yeah, I guess you'd be happy with that...”

“Oh, don't beat yourself up.” the crossdresser says, slapping their palm into your shoulder in a friendly manner. “You act like you're the first guy to have feelings for a guy that looks so cute and fluffy. You really gotta explore yourself a little more.”

“I mean, you've seen the stuff I write, right? There's a lot going on up here.”

“And yet all you can focus on is a dinner date with me.”

“I mean...you look great.” you say, trying to change the subject slightly. “Did you pick out the outfit, or was that my head?”

Astolfo smirks at you. “That's my little secret.” He then winks before grabbing a fork and chowing down on whatever it is that's sitting on your plate.

“Sorry,” you say as you rub your head, “it's not very often that I get to talk to someone that's also aware of the dream world, so I was hoping for some answers.”

“No need to be sorry, dude.” says the pink haired Rider. “But I think we both know what it is we're here for, right?” He grins at you again, slowly rising up from his seat. “I mean a dinner date is fine and all, but this isn't any different from last time. You know what you want, I know how to get you what you want...”

The pink haired Rider approaches you, with your seat moving out from the table all on its own. He lifts his leg up high as he swiftly sits on your lap, sucking on his lower lip as he raises an eyebrow up in a seductive motion. "Wait, are you…are you seriously doing this? Here? Now?" you ask, looking at all the other patrons that are dining around you.

"They aren't paying us any attention anyway." Astolfo reminds you, running his finger over your chest. "It's a dream, silly. I keep telling you this, but it never seems to stick to you."

"Right, you've got a point, but that still…hmmmmph…"

Your words are cut short as Astolfo leans into you, pressing his lips against yours while sliding his tongue inside your mouth. Your eyes are shut as he does so, yet you can't help but focus on his lips, which has a very unusually distinct flavor to them. It's fruity, rather addicting, really. "Is that cherry lip gloss?"

"Ohooo, you've noticed." says the Rider, smiling joyfully. "I didn't think you could actually taste things in dreams." You honestly aren't sure either, as it could be a trick your brain is playing on you, but that doesn't matter as the crossdresser presses against your lips once more, with the scent of cherries rising into your nostrils. It's such a sweet taste that the crossdresser has given to you, savoring it while your hands go right for his hips. You squeeze into them tightly, causing Astolfo to hum lovingly into your mouth, his tongue slipping around yours repeatedly.

Seconds later, you start to feel a draft against your lower body. Looking down while Astolfo covers your cheeks in cherry kisses, you see that you're missing your pants, with your cock rubbing against the Rider's. His panties are nowhere to be seen, with the skirt of his dress pushed up enough to reveal his cock to you. A groan escapes through your teeth as your shaft hardens up, with the Rider leaning into your neck for passionate kisses, his tongue lashing away at your skin. The tender loving causes you to lower your hands onto his ass, squeezing his cheeks tightly enough that his entire body jolts.

"Oh shit…" Astolfo whimpers, his lips quivering. "Careful, I'm really sensitive there."

"Oh, you want -me- to be the careful one?" you ask, a grin curling onto your mouth. "I think now's as good a time as any for me to take charge, don't you?"

"You have no idea how long I've waited to hear you say that tonight…" Astolfo says, standing up over your lap. You grab hold of your cock, which had become hard after all the grinding your dream partner has done, and allow him to sit atop it, guiding your crown into his asshole. You watch his face scrunch up, heaving through his nostrils as he squats back down onto your lap, with your inches slowly vanishing into his rectum.

"Fuck, it's surprisingly tight…" you moan. "I thought you'd be used to this by now."

"It's been months you jerk…" Astolfo moans, his cheeks blushing as he looks away from you. "B-Besides, you're the one making the dream, it's probably your unconsciousness keeping it so small."

The Black Rider wraps his arms around your shoulder, while you guide his hips into a rhythm that's to your liking. Once her goes at a slow and steady pace, you move your hands up to the rim that keeps the top of his silver dress in place, unbuckling it to drop down and leave him topless. You lean into his slender chest, lips ready to suckle on his petite nipples. Astolfo coos as you grind your teeth down, while his hips go against you with a slow impactful push as a result.

"You really like my nipples, don't you?" Astolfo asks you, saliva dripping out of his lower lip. "God, it's always the sensitive bits…" The Rider holds your head close to his bosom, allowing you to use your mouth and tongue to play with his nubs. You start to feel his five inch member, now as stiff as yours, gliding against your skin while the tip pokes at your crotch, leaving a wet spot creates by the precum that oozes out. The sounds he makes as you swirl your tongue on his nipples are like bothing you've ever heard before, making you laugh a little. His hips continue to swing along your member, having reached as far up as it can while you give his cheeks another squeeze.

A few more minutes pass, or what feels like it in this dream, before you lift Astolfo off your lap, with your cock popping out of his asshole after he gives another thrust forward. You help him to his feet, watching as his legs wobble slightly while he tries to regain his balance. After you sit up, you hold onto his shoulders and spin him around to face the table, bending him over so that his bare chest is atop it. Surprisingly, your plate of food has vanished, as if it had never been there in the first place. You don't worry about that, as you fins yourself too busy guiding your cock up Astolfo's anus, watching as it vanishes in almost no time. "Looks like you're mote adjusted to my dick." You say to him.

"It doesn't feel like it…" grunts the crossdresser, his hands clawing into the table cloth. You start to pound away at his cute backside, looking around the dining room to see that nobody is giving you even an uncomforting or judgmental stare, as if they were never really there in the first place. Content with that, you continue to ram into Astolfo's ass, hearing the Rider panting loudly while he continues to dig his fingernails into the cloth.

Deciding to play a little rougher with your dream date, you grab hold of Astolfo's braided hair, yanking from the bottom before wrapping it around your palm. You get a little thrill hearing the crossdresser gasp as you tug him back, utilizing his pink braid as a pulley. When your hand ends up where the braid meets the skull, you see Astolfo stare up at you, his face upside down given the angle. You see a trail of saliva coming from his lip, his cheeks as rosy as the flowers that decorate the table, and his eyes begging heavily for release. You grin, deciding to egg him on for once. "Does daddy princess love his cock?" you ask in a teasing manner.

"Yes…" Astolfo squeals. "I love daddy's cock…I love it…I want it to make me cum!"

You slap harder against his body after that, with your shaft grinding over his prostate enough that he finds his cock twitching. The crossdresser is aware that he's bound to cut, although you're only just now reaching that point. With one hard thrust you hold Astolfo close to your body, wrapping your arms around his torso just as the first burst of cum floods its way into his rectum.

Astolfo grips the table cloth tightly, enough to pull it off the table and bring whatever is remaining on there crashing to the ground. Still nobody turns to see what the commotion is about, even as you're too preoccupied with unloading your seed into the Rider's anal cavity. He growls through his teeth while his hole is flooded with the substance, his cock already blasting out its own juices onto the pristine white cloth. The crossdresser leaves an obvious stain on there, with a gooey cum puddle forming right on top of it.

When you pull your member out of Astolfo's backside, the Rider's upper body collapses onto the table, having enough strength to grab his ass cheeks and spread them out. You laugh as you see your Spink dropping out of the anus, making a mess right on the floor, again to the care of nobody else in the dining area.

"That…that was so good…daddy…" Astolfo moans, embarrassed at how easily that rolled off his tongue.

"Heh…let's not do that all the time." You say, leaning in to peck at Astolfo's cheek. You give his cheek another tight grip, watching as his back arches, with his legs raised into the air thanks to leaning onto his tippy toes.

"Damn you…" he groans. "That was really good…"

There's a long pause as you start to feel things fading away, including the room and the crossdresser. It seems you're about to wake up from your little dream, hearing one thing before you return to your reality.

"Promise me you won't take so long next time…"

**Author's Note:**

> Hope you enjoyed this story, folks. Let me know what you think with comments, please.


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